The Slumberland Files: Teacher's Rules

by DougtheLoremaster

Rating: mature
Tags: Porn, My Little Pony: Friendship is Magic, Fetish, Romance, Sex, Spoiled Rich, Cheerilee, Alternate Universe
Length: 2593

Two mares, each with animosity towards the other. Can they find common ground in a magical realm where anything goes?

In an alternate reality, the popularity of ponies and creatures of the My Little Pony Television Show is directly tied to their social status in the realm of Equestria. Celestia, the ruler of the realm, has passed a law dictating that a pony's popularity is directly tied to how much sex they are allowed to enjoy each day or night. The royalty; Celestia, Luna, Twilight, and Cadence are all in the lap of luxury as are the rest of the Mane 6 (Applejack, Pinkie Pie, Rarity, Fluttershy, Rainbow Dash, Starlight). What about those the community has forgotten or perhaps flat out ignored? What should they do about their pent up frustration?

Unbeknownst to her sister Princess Luna has opened up a special realm within the World of Dreamers. This realm will secretly allow any pony to violate the law of sexual prohibition for the lower class and allows the entrant to live their deepest desires, whatever they may be. To enter this underground dungeon, a pony or creature must simply dream of themselves saying the following phrase. "Luna is best Princess."

Many ponies as well as other creatures have traversed through the doors to this fantasy realm. This is one such tale. Remember, though, what occurs in this realm must never see the light of day. For that is the way of Slumberland.

Cheerilee is a top 100, who is being tormented by her student Diamond Tiara. And when her services are requested by none other than Spoiled Rich; Diamond's mother, she will have to put aside her biases in order to fulfill a magical assignment by Princess Luna. Can she do it?

Published 2022-04-15 02:10:01 UTC
Last updated 2022-04-15 02:10:01 UTC

Just solve the equation

Cheerilee gave a groan as she threw her keys on the table; another day of teaching her delightful little students had come to a close. She loved teaching the little fillies and colts but lately, one particular student was wearing her down. Diamond Tiara.

Diamond Tiara was a bully, rude and mean to not just the other students but also very disrespectful to her, as well. Her mother, Spoiled Rich, was not only a head of the school board, she was the head of the school board. And so Diamond openly bragged about her ability to do whatever she wanted. Cheerilee was sick of it; Diamond refused to sit still in class or play nice with others. Cheerilee just wanted to cry.

Trudging through the doorway to her bedroom, she did a double-take; there on the bed was a Navy Blue envelope with a large ‘L’ on it. Eyeing it incredulously, she winced. Like most of the top 100, she eagerly signed up to work for Luna and help out those not on the list. They had needs too, after all. And unlike teaching, it paid well.

But she was horribly sore after the last client, a stallion, decided to be an ‘alpha male’ and see ‘how much she could take’. Ever since that law got passed, Cheerilee had been entertaining fantasies of stallions left-right, and center, Night after night, she would find herself getting railed from behind as the mattress shook. So much for a night to myself. She sighed and went over to her bed, and climbed in under the covers, before closing her eyes. Best see what Luna wants from me, Luna is best princess.

Upon thinking those four words, Cheerilee found herself in a vast gallery of paintings; each depicting a rather explicit scene between many forgotten ponies and the top 100’s. Walking towards the middle of the room, Cheerilee approached a receptionist's desk, behind which sat the Lunar Princess, herself.

Cheerilee watched in amazement at all the well-knowns preparing for their nightly assignments. Trixie grabbed Twilight’s hoof and pointed excitedly at her letter, as Twilight rolled her eyes and broke into a grin.

“Sounds scandalous, I’m in.”

Spitfire was talking to a pink earthpony with a dark red mane and on the mare’s flank was a root beer float.

“You really want that? Yeah, sure, I can do that easily…Ahem well shall we start?”

Barely waiting for a second, Spitfire roared at the hapless Earthpony.

“Welcome to the Wonderbolts Bootcamp, Soda Float, this night will be the most miserable three weeks of your life. Straighten up! On your hooves, soldier! Back straight, head forward, spit out that gum!”

Cheerilee watched as Spitfire smacked Soda Float’s flank causing her to spit out a wad of gum in surprise. She chuckled; anything and everything was fair game in this realm, from deepest to darkest desires, nothing was off-limits. Finally, she arrived at the desk to find Luna beaming at her.

“I’ve got a client who practically begged to see you.”

“Really?”

“Oh yes, and I think you’ll find this rendezvous quite special.”

“So who’s the stallion this time?”

“Who said anything about a Stallion?”

Cheerilee raised an eyebrow, intrigued.

“Oh?”

Standing outside the door to her classroom, Cheerilee looked down at the fantasy description in her hooves. It was a standard naughty schoolfilly fantasy; caught being bad, called to the front, and punished by the teacher in front of the classmates. Humiliation fetish; Typical, nothing new, what made Luna claim it would be special? Whose fantasy was this anyway? Glancing at the signature at the bottom of the parchment scroll, Cheerilee blinked in surprise. Surely this was some joke, or maybe she was reading it wrong. There was no way her client was that mare.

She sighed and ran her forehoof through her mane, glancing down at her debutante outfit, a short miniskirt that just barely covered her features, the delightful lack of exposure; the lacey rose-print cotton panties. She gritted her teeth. She was a professional; whoever the client or whatever the desire, she would provide. Even if it was her. Let’s do this.

Taking a deep breath, Cheerilee pasted a stern expression on her muzzle and applied some lipstick before throwing open the door and strutting through it. Without so much as a glance at the desks, Cheerilee faced the chalkboard calling out loudly as she wrote her name on it.

“Settle down class, my name is Mrs. Cheerilee. And-”

She spun around to face the classroom, in which sat nine of her students and Spoiled Rich; dressed in a regulation filly school outfit. She certainly dressed for the part. Alright, so she is serious. Staring directly into Spoiled Rich’s baby blue eyes, she lowered her voice to be silky and dangerously seductive.

“I’ll be teaching-”

Placing a hoof under Spoiled Rich’s chin and gently raising it up, Cheerilee whispered softly.

“You.”

Leaning in, as if for a kiss, Cheerilee watched as Spoiled Rich expectantly closed her eyes before leaning forward to meet her lips; only for Cheerilee to stand up and whirl around just as they were about to connect. Spoiled lurched forward onto her desktop in surprise.

“I have three rules in my class. One-”

Picking up a rigid yardstick, Cheerilee emphasized her points with a swift strike to the chalkboard.

Bwap!

“No chewing gum in my class. Two-”

Bwap!

“No talking without being called on! And three-”

Bwap!

Whirling around, Cheerilee slapped the yardstick on Spoiled Rich’s desk causing her to jump.

“-You will refer to me as Mrs. Cheerilee. Understood?”

Spoiled Rich felt a bead of sweat roll down her cheek, this Cheerilee was far more assertive than her normal, and she loved it. She eagerly exclaimed.

“Yes, Mrs. Cheerilee!”

Cheerilee turned to face the chalkboard, allowing a secret smirk of satisfaction to grace her lips, before picking up her chalk and reaching up, allowing her skirt to just crest the top of her rose-print panties; revealing the dainty pattern. Behind her, she could feel the hungry stare of Spoiled Rich on her flank. Swiftly, Cheerilee wrote an impossible-to-solve equation on the board, one that made no sense as she called out.

“Alright class, take out your mathematics books and turn to page 42.”

In a flurry of sound, Cheerilee listened as books were placed onto desks and her class turned the pages, counting silently to three before turning and calling out at a hapless Spoiled Rich.

“Young mare! Where is your book?”

To really sell the humiliation aspect, her class had been given books to pull forth, all except Spoiled that is. Spoiled Rich went as white as a ghost as she started to look around in a panic as the class of colts and fillies taunted her in a childish singsong voice.

“Oooh, you’re in troub-ble~”

Like a deer in the headlights, Spoiled was caught completely off-guard and began to stammer.

“I-I didn’t- I mean I- I-”

Cheerilee wore a mock scowl as she shook her head.

“No excuses young mare, get up to the board. Now.”

In a panic, Spoiled rushed up to the chalkboard, only to receive a sharp smack across her left flank with the yardstick, causing her to jump. Wincing, she looked at Cheerilee who snapped at her.

“That’s strike one.”

“B-but I-”

“Focus on the board, not me. What do we do first?”

Looking at the board, Spoiled Rich stared at the drawing of a duck, with a shooting star under a square root, being multiplied by a hoof full of gumballs subtracted by 5 and being divided by a fraction of the sun over a crescent moon plus 42.

“Uh-”

*Smack!*

“Ow!”

“No shouting in my class, and straighten up!”

Sliding the yardstick between Spoiled’s hindlegs, Cheerilee jerked it up, to rub roughly against Spoiled’s velvet slit, causing her to wince and stiffen up. Noticing the ease with which the yardstick slid across the moist surface, Cheerilee continued, as though nothing happened.

“That’s better. Now tell me, what do we do first?”

“Um, divide by the sun?”

*Fwap!*

“Eep! Um, I-”

Cheerilee shook her head dismissively as Spoiled whimpered in a panic. Calmly she reached out and grabbed Spoiled’s hoof in her own while positioning her other hoof around Spoileds waist. Forcibly guiding her hoof she said.

“First we figure out the square root of the odds of a shooting star, which is 84%, we will then add that to the number of feathers on a full-grown duck.”

Spoiled’s face was a bright cherry of embarrassment as Cheerilee leaned slowly into her face.

“That’s 11903, by the way. Which gives us 21,901. Now if we divide by the days in a year, represented by the sun, that’s 364 and divide that…”

Her voice trailed off as she stared into Spoiled’s eyes.

*Bwap!*

Like lightning, Cheerilee swiftly smacked Spoiled’s flank with enough force to cause it to ripple. Spoiled gave an unabated moan as Cheerilee said sternly.

“Focus on the board, you’ve almost finished. Now divide by the phases of the moon, there are 8.”

As she spoke, Spoiled’s body trembled and she winced as she wiggled her flank in an almost frantic motion. Cheerilee shook her head.

“Not yet, little mare.”

Reaching across, Cheerilee gave the opposite hindquarters a large smack, watching the ripple in satisfaction as she said simply.

“I have not given you permission, now focus!”

Another series of light spankings across both of Spoiled’s cheeks in rapid succession caused Spoiled to whimper more frantically as she tensed the muscles in her hindquarters, desperately trying to focus on the board. Cheerilee leaned in and whispered in her ear slowly, silkily.

“I know you can do it.”

Straightening up, Cherilee continued, sliding the yardstick once more against Spoiled’s inner sanctum, sliding it effortlessly across the audibly dripping lips.

“Now we divide that by the phases of the moon and we get 7.5, now we round that up-”

Jerking the stick to slide into Spoiled’s special place, Cheerilee smirked as the mare let out an audible gasp, mixed with a whine and moan. Spoiled’s body trembled and shook as she neared her limit. Frantically she winced and tightened her muscles even more going as rigid as possible.

“To 8 which when we subtract the number of gumballs on the board we get a total of 2. So the answer is…”

Practically squealing between gritted teeth, Spoiled rich answered.

“Two. The answer is two!”

“Very good, now-”

Leaning in close, Cheerilee’s voice dropped low and took on a silky, tender tone.

“Go ahead and come for me, my little-”

Just before locking lips with Spoiled’s own, Cheerilee whispered.

“Mare.”

At once, as she melted into the kiss, Spoiled Rich let the dam burst; allowing the feeling of ecstasy to wash over and overwhelm her, her inner demons of stress fleeing her sacred temple in droves. The last thing she saw before darkness rushed in was Cheerilee’s smiling face.

*Chink*

“Hrungh?”

Spoiled Rich blinked, sitting up to look around at the sound of a lighter being lit.

“Oh, good, you’re awake.”

“What’s going on? Where am I?”

Cheerilee sighed as she lit the cylindrical object in her hooves.

“The employee lounge. You were so excited you literally passed out. I was worried, so I brought you back here with me.”

“Oh, well thank you, I had a lovely time by the way.”

Taking a long drag on the ash-filled cylinder in her hoof, Cheerilee averted her eyes and grumbled.

“Yeah, sure. Whatever.”

“What? I was saying thank you for-”

“Look Spoiled, you don’t have to pretend to be nice to me anymore.”

“I…I’m not pretending, Cheerilee I really did have fun.”

“Stop lying. You got what you wanted and I gave you your little fantasy. Sheesh! What is it with you and your daughter and lying?”

“Wha…I’m not lying! Wait. What about Diamond? What are you talking about?”

Cheerilee threw down the cylinder and shouted at Spoiled.

“Like you don’t know. Little Miss ‘My mom is head of the board. I can have you fired anytime’. I’m sick of it, Spoiled.”

Spoiled looked stricken before rising up off the sofa and wrapping her hooves around Cheerilee in a warm embrace. Speaking gently, the normally holier-than-thou attitude of Spoiled Rich was nowhere to be seen.

“Did Diamond say that to you?”

Cheerilee whimpered as a tear slid down her cheek, melting wantingly into the embrace, Cheerilee nodded. Closing her eyes, she expected shouting, insults…anything. But it never came. Opening her eyes, Cheerilee was surprised as Spoiled stole a kiss, before staring her in the eyes.

“Tell me everything.”

Walking into her classroom, Cheerilee flinched as Diamond Tiara taunted her.

“Look who’s late, have you forgotten I can have you fired in a-”

“Is that so?”

All eyes turned to the doorway, in which stood an angry Spoiled Rich; her eye twitching in annoyance. Diamond Tiara began to stammer.

“M-mom? I was just-”

“No Diamond. That may fly with your father, but not me. I came here to watch your class and imagine my surprise when I hear my own daughter using my hard-earned title for clout.”

Diamond Tiara looked like she wanted to be anywhere else, as her mother berated her in front of the class. But Spoiled wasn’t done yet.

“Tell me again, Miss Cheerilee, how many assignments have my daughter failed to turn in?”

Cheerilee looked surprised but replied thoughtfully as Spoiled approached her.

“All of them, almost two hundred, I would say. Mrs. Rich.”

Coming to a stop at Cheerilee’s side, Spoiled Rich secretly slipped her an envelope with a large ‘L’ on it and spoke out loud for all to hear, as she passed judgment on Diamond Tiara.

“Well then, considering she has until the end of the week to turn them all in, I suggest my daughter refrain from hanging out with her friends and mind her P’s and Q’s around you; putting that snout of hers to the grindstone. No TV, no sleepovers, no shopping.”

Diamond squealed out.

“But mom!”

Spoiled Rich continued staring at her daughter.

“No anything, until those assignments are all accounted for and you can bet I’ll be checking every answer to ensure they are done right. Furthermore, I insist that you will be attending Cheerilee’s Summer School and woe betide your flank if you ever mistreat her again.”

Cheerilee sat at her desk staring down at the envelope given to her by Spoiled Rich. Classes were over for the day, and there had been no further outburst from Diamond Tiara since the morning. Tearing open the envelope, she pulled out a letter that smelled of lilacs and roses. Pulling open a drawer on her desk, she pulled forth her reading glasses. Placing them on her face she read the following:

Cheerilee,

It meant the world to me the consideration and loving care you put forward to satisfy me, and though I don’t usually write letters, Princess Luna insists it be done, so here I am trying to pen my thoughts on parchment at midnight.

Last night was the first time in many years that anypony touched me, and made me feel like a real mare; catering to my desires and wants. Even before the law was passed, Rich had a wandering eye and for all but me, we haven’t been intimate since Diamond was born. Thank you, for a truly magical evening and if possible, I would love to enact a few of your fantasies as well.

-Spoiled Rich